Advanced Synthesis and Catalysis
Advanced Synthesis and Catalysis
5 years ago

Stereoselective Mannich Reaction of N-(tert-Butylsulfinyl)imines with 3-Fluorooxindoles and Fluoroacetamides

Stereoselective Mannich Reaction of N-(tert-Butylsulfinyl)imines with 3-Fluorooxindoles and Fluoroacetamides
Buquan Zheng, Jianbo Zhao, Ya Li, Xinfeng Ren, Xiangyu Chen, Qi Lu
A diastereoselective Mannich reaction has been developed for the construction of stereogenic C−F units by the reaction of α-fluoro-substituted amides, including highly activated 3-fluoro-oxindoles, and simple linear fluoroacetamides with N-tert-butylsulfinylimines. This method provides a concise route to a variety of structurally diverse α-fluoro-β-amino amides containing stereogenic fluorinated carbon centers. This protocol has the benefit of using readily accessible starting materials and is operationally simple. The Mannich reactions of cyclic and linear α-fluoro-substituted amides resulted in different stereochemical outcomes, suggesting that these substrates reacted via closed and open transition states, respectively.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700353

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